期刊
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
卷 78, 期 3, 页码 232-239出版社
SOC SYNTHETIC ORGANIC CHEM JPN
关键词
metal nanoparticle; quinone; hydrogenation; continuous-flow system; hydroquinone derivatization; reaction integration
Several single metal and bimetallic nanoparticle catalysts immobilized on polymer supports have been developed for selective hydrogenation of quinones to hydroquinones. Au-Pt bimetallic nanoparticle catalyst showed the best reactivity and selectivity for this purpose. Though slight over-reduction proceeded under batch conditions, higher reactivity, selectivity, and robustness of the catalysts were confirmed under continuous-flow conditions with polydimethylsilane-supported catalysts. Various direct derivatizations of quinones, such as methylation, acetylation, trifluoromethanesulfonylation, and benzoylation were successfully performed under sequential-flow conditions to afford the desired products in good to excellent yields. Especially, air-sensitive hydroquinones, such as anthrahydroquinones and naphthohydroquinones, could be successfully generated and derivatized under closed sequential-flow conditions without decomposition. This sequential-flow systems showed various benefits of flow systems; suppression of over reactions by controlling residence time, facile use of unstable intermediates, continuous production and robustness of the system.
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